(1S)-1-C-(2-amino-4-hydroxypyrrolo[3,2-d]pyrimidin-7-yl)-1,4-dideoxy-1,4-imino-D-ribitol | 209799-75-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: (1S)-1-C-(2-amino-4-hydroxypyrrolo[3,2-d]pyrimidin-7-yl)-1,4-dideoxy-1,4-imino-D-ribitol
• 英文别名: Immucillin G；2-amino-7-[(2S,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]-3,5-dihydropyrrolo[3,2-d]pyrimidin-4-one
• CAS: 209799-75-7
• 化学式: C₁₁H₁₅N₅O₄
• 分子量: 281.271
• InChiKey: KBIDJCVAURJXFG-PVEDRDFWSA-N

物化性质

• 沸点：
  656.4±65.0 °C(Predicted)
• 密度：
  2.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  156
• 氢给体数：
  7
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-O-tert-butyldimethylsilyl-1,N-dehydro-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol 在 palladium on activated charcoal 氨 、 氢气 、 sodium acetate 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 75.5h， 生成 (1S)-1-C-(2-amino-4-hydroxypyrrolo[3,2-d]pyrimidin-7-yl)-1,4-dideoxy-1,4-imino-D-ribitol
  参考文献：
  名称：

  Synthesis of Transition State Analogue Inhibitors for Purine Nucleoside Phosphorylase and N-Riboside Hydrolases

  摘要：

  Syntheses of the 'Immucillins', potent aza-C-nncleoside inhibitors of purine nucleoside phosphorylase are reported as well as those of 5-deoxy-, 5-deoxyfluoro- and 2-deoxy- analogues and others having modified bases. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00194-0

文献信息

• Pyrrolo-thiazines and processes for the preparation and use thereof
  申请人：Hollingsworth Rawle

  公开号：US20070055062A1

  公开（公告）日：2007-03-08

  1H-Pyrrolo-1,4-thiazines and a process for the preparation thereof are described. These compounds are useful as enzyme inhibitors in cells, particularly for medical uses.

  描述了1H-吡咯并噻嗪及其制备方法。这些化合物在细胞中作为酶抑制剂具有用途，特别适用于医疗用途。
• Compositions for treating or preventing obesity and insulin resistance disorders
  申请人：Sinclair A. David

  公开号：US20060111435A1

  公开（公告）日：2006-05-25

  Provided herein are methods and compositions for modulating the activity or level of a sirtuin, thereby treating or preventing obesity or an insulin resistance disorder, such as diabetes in a subject. Exemplary methods comprise contacting a cell with a sirtuin activating compound or an inhibitory compound to thereby increase or decrease fat accumulation, respectively.

  本文提供了一种调节sirtuin活性或水平的方法和组成物，从而治疗或预防主体的肥胖症或胰岛素抵抗障碍，例如糖尿病。示例方法包括使用sirtuin激活化合物或抑制化合物接触细胞，以此分别增加或减少脂肪积累。
• Inhibitors of nucleoside metabolism
  申请人：——

  公开号：US20020061898A1

  公开（公告）日：2002-05-23

  The present invention provides novel nucleoside-analogue compounds that are effective inhibitors of purine nucleoside phosphorylase (PNP), purine phosphoribosyltransferases (PPRT), and/or nucleoside hydrolases. Also provided are tautomers, esters, prodrugs, and pharmaceutically-acceptable salts of the compounds disclosed herein. The present invention further provides the use of these compounds as pharmaceuticals. The present invention also discloses pharmaceutical compositions containing these compounds. Finally, the present invention provides processes for preparing these compounds.

  本发明提供了新型核苷类似物化合物，它们是嘌呤核苷酸磷酸酶（PNP）、嘌呤磷酸核糖转移酶（PPRT）和/或核苷水解酶的有效抑制剂。此外，还提供了这些化合物的互变异构体、酯、前药和药学上可接受的盐。本发明进一步提供了这些化合物作为药物的用途。本发明还揭示了含有这些化合物的制药组合物。最后，本发明提供了制备这些化合物的过程。
• AZA nucleosides, preparation thereof and use as inhibitors of RNA viral polymerases
  申请人：Babu S. Yarlagadda

  公开号：US20070099942A1

  公开（公告）日：2007-05-03

  Compounds represented by the formula: , and pharmaceutically acceptable salts thereof and prodrugs thereof; wherein R 1 is H, CH 3 , C 2 H 5 , C 3 H 7 R 2 is H, CH 3 , C 2 H 5 , C 3 H 7 , CH═CH 2 , CH 2 —OH, CH 2 F, CF 3 R′ 2 is H, OH, NH 2 , NH-alkyl, F, N 3 , OCH 3 , O—C(O)CH(NH 2 )alkyl R 3 is H, CH 3 , C 2 H 5 , C 3 H 7 R′ 3 is H, OH, NH 2 , NH-alkyl, F, N 3 , OCH 3 , O—C(O)CH(NH 2 )alkyl R 4 is H, CH 3 , C 2 H 5 , C 3 H 7 At least one of R 2 , R 3 , or R 4 has to be other than H, when X═NH in B R 6 is H, CH 3 , C 2 H 5 , R 7 is selected from H, alkyl, alkenyl, aryl, acyloxyalkyl, and pivaloyloxyalkyl, aminoacids, CH 2 CH 2 SC(O)alkyl; and B is represented by the following structure: X is independently NR 6 , O, S, R 8 and R 9 independently is H, NH 2 , OH, SH, F, Cl, Br, I, aryl, heterocycle, alkyl, alkene, alkyne, S-alkyl, S-aryl, S(O)-alkyl, SO 2 -alkyl, SO 2 NH 2 , SO 2 NH-alkyl, SO 2 NH-aryl, NH-alkyl, NH-aryl, N(alkyl) 2 , N(aryl) 2 , O-alkyl, O-aryl, O-heterocycle, NH-(CH 2 ) n -aryl, NH—C(O)-alkyl, NH—C(O)-aryl are useful for inhibiting viral RNA polymerases and treating patients suffering from diseases caused by various RNA viruses.

  该化合物的结构式为：其中R1为H，CH3，C2H5，C3H7；R2为H， ， ， ，CH═CH2， —OH， F，CF3；R′2为H，OH，NH2，NH-烷基，F，N3，O ，O—C（O）CH（NH2）烷基；R3为H， ， ， ；R′3为H，OH，NH2，NH-烷基，F，N3，O ，O—C（O）CH（NH2）烷基；R4为H， ， ， 。当X═NH时，R2、R3或R4中至少有一个不为H。BR6为H， ， ；R7选择自H、烷基、烯烃基、芳香基、酰氧烷基和哌酰氧烷基、氨基酸、 SC（O）烷基；B的结构式如下：其中X独立为NR6，O，S；R8和R9独立为H，NH2，OH，SH，F，Cl，Br，I，芳香基，杂环，烷基，烯烃基，炔基，S-烷基，S-芳香基，S（O）-烷基，SO2-烷基，SO2NH2，SO2NH-烷基，SO2NH-芳香基，NH-烷基，NH-芳香基，N（烷基）2，N（芳香基）2，O-烷基，O-芳香基，O-杂环，NH-（ ）n-芳香基，NH—C（O）-烷基，NH—C（O）-芳香基。这些化合物可用于抑制病毒RNA聚合酶和治疗由各种RNA病毒引起的患者。此外，还包括这些化合物的药物可接受的盐和前药。
• Methods and compositions for treating flushing and drug induced weight gain
  申请人：Sinclair David

  公开号：US20060276416A1

  公开（公告）日：2006-12-07

  Provided herein are methods and compositions for treating and/or preventing flushing and/or weight gain. Methods may comprise modulating the activity or level of a sirtuin, such as SIRT1 or Sir2. Exemplary embodiments include methods and compositions for counteracting drug-induced weight gain and/or drug-induced flushing by administering a sirtuin-activating compound.

  本文提供了用于治疗和/或预防面部潮红和/或体重增加的方法和组合物。方法可以包括调节sirtuin的活性或水平，例如SIRT1或Sir2。示例实施方式包括通过给予sirtuin激活化合物来抵消药物引起的体重增加和/或药物引起的面部潮红的方法和组合物。